A very young looking Frank Sinatra appears on television for the first time on May 27, 1950, trading jokes and barbs with Bob Hope on the latter’s television show. Already well established as a singer, Sinatra made his presence known in Hollywood when he won the Academy Award for Best Supporting Actor in 1953 for his role in From Here to Eternity.

Clive James interviews Sinatra about his love for singing and the video shows clips from opening acts and a song from Sinatra who is called the “most famous man in the world.” In 1988, Frank Sinatra travels to Australia to perform at the Sanctuary Cove concert, 14 years after he vows never to return to that country because of negative comments about him in the press.

Fellow entertainers attend Frank Sinatra’s memorial, with Wayne Newton, Debbie Reynolds, Joey Bishop and more talking about Sinatra’s legacy. Historian Rick Ross also chimes in and Jerry Lewis is a noted no-show. Sinatra, a singer and actor, died on May 14, 1998 and was eulogized by his son, Frank Sinatra, Jr.

Bill Newcott interviews Frank Sinatra, Jr. for My Generation inside the Capitol Records building in Los Angeles where Frank Sinatra recorded much of his music. The two discuss some of Frank’s more famous friends, including Dean Martin; how the world of music changes in the 1960s with Elvis Presley’s music plus the British Invasion; how Frank Sinatra, Jr. served as his father’s musical director for the last 7 years of his concert performances; and more.

Frank Sinatra was well-known to many people and when he passed away on May 14, 1998, many of them discussed his legacy with Larry King: his daughter, Nancy Sinatra; Mia Farrow; Joey Bishop; Shirley Jones; George Schlatter; Eartha Kitt; and Vic Damone.

Nancy Sinatra talks about her close relationship with her father, Frank Sinatra. Her dad, Frank Sinatra, passed away on May 14, 1998: "I miss that I can't pick up the phone and say, 'Daddy what do I do about this?'"

Frank Sinatra, Jr. talks about how he became close to his father when he became his Music Director in 1988. He talks about his dad's fame: "When the legend becomes bigger than the person, you lose the person. And this is not good…" Frank Sinatra, Sr. passed away on May 14, 1998.

One night in the 1960s, Larry King and friends were talking about what would be impossible to make happen in their relative careers and King shares that it would be impossible to get Frank Sinatra on his radio show–his friend Jackie Gleason told King that he would get him Sinatra. King went on to interview Sinatra quite a number of times in his career and Sinatra's last television interview was on Larry King Live. Sinatra passed away on May 14, 1998.

Marilyn Monroe talks briefly about how she did not like Frank Sinatra when he was a "bobby soxer" but liked his style as an adult. The two had a short-lived affair in 1961 after Sinatra's marriage with Ava Gardner had ended in 1957. Sinatra passed away on May 14, 1998.

American entertainer Sammy Davis Jr. answers questions about Frank Sinatra while in Palm Springs during a Charity Golf Tournament. Davis talks about Sinatra's kindness, star power, and dedication. Frank Sinatra was born on December 12, 1915.